マディソン郡にあるバケーションレンタル

Aerie Loft Apartment with view that sleeps 7

This elevated second story apartment has an incredible view of the historic downtown square and courthouse. Bring your group to be in a centralized location near dining/bars , shopping, museums, and a movie theatre. Accommodations for a group of seven is ideal for getaways or special occasions. The unique relief art sculpture of a tree and eagles will captivate you. A full kitchen with all the essentials. 6 beds and spacious 3/4 bath and a second 3/4 bath opened for 5 or more guests.

Charming abode

Soft natural light fills the living spaces, creating a bright and cheerful atmosphere that instantly makes you feel at ease. The living area offers cozy seating and a calm, inviting feel—perfect for relaxing after a long day. A place where laughter is shared, memories are made, and every day feels a little more relaxed. Whether you’re spending quality time with family, hosting friends, or enjoying peaceful moments on your own, this home offers the perfect setting to truly feel at home. Enjoy!

The Legacy Stone House

The most unique stay in Winterset! Legacy Stone House AirBnB is a historic residence located one mile east of Winterset, Iowa. Built in 1856 during the Settlement Era of Madison County, it is one of nearly 100 stone houses built during that time in the area. Officially named the William Anzi Nichols House, it is listed on the National Register of Historic Places. Convenient centralized location if visiting Madison County’s six covered bridges and two minutes from grocery, gas and dining.

Pickleball Barn | Firepit + Hot Tub | Sleeps 14

🏓 PRIVATE PICKLEBALL BARN Indoor pickleball court 9' kid-approved slide (kids LOVE it) Climate-controlled for year-round fun 🔥 OUTDOOR OASIS 6+ person hot tub Large fire pit 12-person outdoor dining table Private 3 acres Gorgeous sunrise/set 🎬 INDOOR ENTERTAINMENT 98" TV in basement living room Foosball, ping-pong, pool table & Pacman 2nd living room upstairs for quiet escapes 🏡 PERFECT FOR GROUPS Sleeps 14 comfortably Multiple hangout zones Great for multiple families + teams

Winterset Square Loft/Retreat

This apartment was created for you to relax, read, write, or create content. Located on the 2nd level of the historic Madisonian building in downtown Winterset. Walkable to coffee, restaurants and shopping. Drive-able to everything Madison County has to offer including the famous covered Bridges. You can pre-order charcuterie to have waiting in the fridge from tenant below (ask host for a link.) Coffee included (Keurig) during your stay or an adorable coffee shop is 3 doors down.

Iconic Iowa - A 1920 Built Country Cabin

This 1920 Log Cabin sits at the beginning of the Madison County covered bridges Scenic Byway and features 2 rural country acres of space and a wonderfully remodeled home with loads of character and style. Situated just 10 minutes south of the West Glen area of West Des Moines and 25 minutes from downtown Des Moines, you'll experience the quiet and beauty of rural Iowa while being close enough for shopping or to go out for a nice dinner or evening show. This is a great getaway.

Hygge House in the ❤️ of historic Winterset

Hygge: a Norwegian word for a mood of coziness, and comfortable conviviality with feelings of wellness and contentment. Swing on the quaint side porch or congregate on the large back deck. Gather at the harvest table in the front room. Cook a meal in the kitchen. Walk the 3 blocks to the historic square and enjoy shops, restaurants, museums and parks or take a bike ride. Bring your girlfriends for a craft weekend or your family and enjoy all our wonderful town has to offer!

Luxury 2 Bed/2 Bath Condo-1 Block to Downtown

Experience luxury in this 2-bedroom, 2-bath condo on Airbnb, designed for relaxation and comfortably sleeping four guests. Highlights include an elegant fireplace for cozy evenings and a fully equipped kitchen for gourmet meals. Nestled in a prime location, this condo promises both comfort and convenience, making it an ideal choice for travelers seeking a blend of luxury and practicality. Enjoy unwinding by the fire or exploring nearby attractions for an unforgettable stay.

Glamping Flower Farm Stay- PepperHarrow

Escape to the beauty and tranquility of PepperHarrow, a 20 acre flower farm in Madison County. Our glamping tent offers a unique and peaceful getaway, surrounded by 8.5 acres of stunning flowers. Relax and unwind amongst 2.5 acres of lavender, 1.5 acres of annuals, 1 acre of perennials, and wildflower areas supporting local pollinators. Experience the magic of nature from the comfort of our cozy glamping tent, perched atop the bluffs overlooking the Middle River Valley.

Friendly Quarters

This charming location is a farmhouse style home built in 1914. Easily found on the main street through town, a one block walk in any given direction will put you at the center of the city. A grocery story, eating establishments, gift shops and community center are conveniently located in the downtown area. Friendly Quarters operates as a non-profit organization to support the missions and ministries of Earlham Friends (Quaker) Church located right next door.

The Roost at Speckled Hen Farms.

Explore the Iowa countryside with this 70's ranch as your relaxing base camp. Situated on 5 acres of rolling hills in rural Madison County, Iowa, this centrally located homestead has something for every kind of traveler. The charming town of Winterset is just minutes away, as well the historic Covered Bridges, wineries, breweries, parks and more. Located next to Speckled Hen Farms farm store and Lone Oaks Farm, you can take in an occasional music event or class!

​Cottage on Court: Historic Gem | 3 Blks to Square

Our renovated 1910 "Cottage on Court" is more than just a place to stay; it’s a home where memories are made. This charming 2-bedroom, 1.5-bath cottage blends historic charm with modern amenities for a perfect stay. Nestled just 3 blocks from the downtown square, you’re close to shops, cafes, and attractions like the John Wayne Birthplace and Quilt Museum. Book your stay today and discover the allure of our charming cottage in the heart of historic Winterset, IA